Mentors are a true career asset, whether they are “officially” part of a formal mentoring relationship (often matched through a mentoring program) or unofficially informal relationships that grow organically. Regardless of how you enter a mentoring relationship it’s important to be intentional about the questions to ask a mentor so you receive the full value from the relationship.
If you’re in an informal relationship that arises out of natural connection, you may find yourself asking questions very naturally, as a part of dialog and connection. This is great, but it’s also a good idea to think about what you’re asking to be sure you’re getting information that really moves your own career aspirations forward. If placed into an official “mentoring relationship,” you may actually experience tinges of anxiety, thinking: what should I talk to them about?
You may also find yourself in mentoring situations you didn’t really plan for. Some events incorporate a “speed mentoring” component intentionally, but there are many opportunities to seek the advice of people with experience and knowledge you could use.
That’s why it’s a good idea to develop questions like these, even if you’re not in an actual “mentoring relationship.” You’ll have some hip-pocket, go-to topics to ask anyone, any time you spot an opportunity to get some mentoring advice.
Where to start your mentoring relationship
While mentoring is most successful when part of a good personal relationship, the actual career value comes when the insight and advice you get from your mentor is highly aligned with your own career aspirations and curiosity.
You probably have some fuzzy ideas of things to discuss with your mentor, but I encourage you to sharpen it up with a focus on your career goals and strategies to get around obstacles in your path. Once you’re as clear as you can be on this, you’ll come up with really pointed and valuable questions to ask a mentor.
Getting clear on your goals:
- Summarize your own career goals
You’ll want to share whatever you know about your goals with your mentor. This will help them think of questions you don’t even know to ask, as well as help them focus their advice. If you’re not totally clear on your goals, this is okay! Part of what your mentor is there to help you with is sharpening up your understanding of what’s possible so you can make choices. In some cases, they may give you information you can’t choose from yet, but they can help guide you to learn more so you can make choices.
A key to sharing whatever clarity you have with them is to describe your goals in positive terms. This means saying, “I do want _________,” or “I may want __________.” The key is not to focus very long on what you don’t want. Although you may have to share things you don’t want, don’t dwell on it. They will be much more effective in helping you to the extent they’re clear on what you’re looking for, instead of what you’re looking to avoid.
Part of this strategy is to remain future-focused. You can certainly share past experiences with them, but direct their attention to ideas you have about the future and don’t get stuck in the past.
- Identify 2-3 (maximum) challenges you have in taking your next step towards your goals
Once you’re as clear as you can be on your goals, identify some things that you know prevent you from reaching them right now. These obstacles may change by job focus and industry, but they often fall into categories like:
- Lack of information and advice
- Confusion or lack of understanding
- Inability to decide based on what you know
- Lack of experience, skills, connections
- Lack of confidence
If these are problems for you, don’t worry about it. These are exactly the kind of things mentors can, and want to, help you with. Take this clarity on your challenges and turn into questions to ask a mentor.
- Research them to find points of connection between their accomplishments and your own interests
As soon as you realize you’re in a mentoring relationship, it’s a good idea to do some research on your mentor. Learn what you can about their background and current responsibilities. Come up with some questions about their career experience as well as their points of view. Just follow your natural curiosity. They will appreciate the fact that you did some homework and will find it easier to get into a discussion with you since you’re not asking them to start from scratch in introducing themselves to you.
Questions to ask a mentor
Now you’ve got an agenda! You are showing up prepared to equip your mentor to help you. Once they have a clear understanding of what you are interested in achieving and the challenges you experience today, their advice will flow more readily and more naturally. You’ll also feel more intentional and directed, which will help you come across well.
You’ll want to kick off with some starter questions, designed to get the conversation going once you’ve shared your goals. Here are a few examples:
- Tell me about how you managed your career when you were at the same point I’m at now: what worked and what didn’t?
- How would you suggest I refine my goals to increase my chances of success?
- If you were me, which of my challenges would you tackle first? Why?
- What do you think is a reasonable form of success for me in the next 6-12 months? What’s unreasonable?
- What was your biggest #career success and why did it work?
- What has been your biggest career disappointment to date and what did you learn from it?
Once you’re into the conversation or relationship, it’s appropriate to go deeper. You’ll want to think about what might happen if you take some of the advice you’ve been given by your mentor (or others) and anticipate the kinds of questions you may have in the future. Or you may want to imagine you make a certain choice and follow it through. What kind of questions might you encounter if you pursue that particular path? Here are some ways to think about deepening a conversation with your mentor.
- If I take your advice to ________, what do you think are the two most likely outcomes? What options might I have if I do this, vs. doing something else?
- If I want to develop skills/get experiences like _________, what are the most effective ways of doing this?
- What do you think are the biggest pros and cons to following path A vs. path B? What would be reasons to pick one path over another?
- Given that I want to do _______, what are the most important technical skills I should develop? What about soft skills? Why are these thing important?
- I’ve had challenges with these kinds of people and situations in the past, how am I likely to encounter them in the future we’re discussing? What’s your advice for using these challenges to handle them more easily?
How to ask great questions (of anyone)
You can see that there are any number of ways to explore the advice and insight your mentor gives you. Learning to start and continue a conversation with your questions is a good life and career skill. Here are a few tips to help you use your mentoring relationship (or any relationship!) to build this important skill.
- Learn to ask open ended questions and try not to ask Yes/No questions. This will help you and others get into a flowing dialog more quickly
- Engage your natural curiosity and think about “what if?” to help you imagine different things you’d like to learn about.
- Fall back often on the question “Tell me more.” Don’t assume that their answers to a question is all they have to say. When you invite people to elaborate on their thoughts they will often come up with surprising and interesting answers to share with you.
Sometimes it seems hard to figure out how to ask good questions, of a mentor or anyone. So here’s a little trick. Make a commitment to spend the next week starting every conversation (or as many as you can) with five minutes of questions before you give an opinion or tell someone what you think.
At first it will seem awkward, but after a day or two you’ll realize you’re listening more carefully to people, looking for things to ask about at the start of the conversation. You’ll also find yourself getting into more interesting and meaningful conversations, which is awesome.
Asking people questions, whether in a mentoring relationship or not, makes them feel that you value and respect them. They’ll tend to open up more and share more information about themselves and the things you’re interested in, more readily.
Try these strategies when you think about questions to ask a mentor, and give yourself the one week challenge to become more curious in all your conversations. See what happens!
